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108-45-2

Basic Information
CAS No.: 108-45-2
Name: m-Phenylenediamine
Article Data: 337
Cas Database
Molecular Structure:
Molecular Structure of 108-45-2 (m-Phenylenediamine)
Formula: C6H8N2
Molecular Weight: 108.143
Synonyms: m-Phenylenediamine(8CI);1,3-Diaminobenzene;1,3-Diaminophenylene;1,3-Phenylenediamine;3-Aminoaniline;C.I. Developer 11;Developer C;Developer H;Developer M;Direct Brown BR;Direct Brown GG;NSC 4776;RT 30H;m-Aminoaniline;m-Benzenediamine;m-Diaminobenzene;N-butyl anhydride;metaphenylene diamine;1,3-Benzenediamine;
EINECS: 203-584-7
Density: 1.15 g/cm3
Melting Point: 64-66 °C(lit.)
Boiling Point: 283.2 °C at 760 mmHg
Flash Point: 147.6 °C
Solubility: 350 g/L (25 °C) in water
Appearance: Gray to white crystal melting
Hazard Symbols: ToxicT,DangerousN
Risk Codes: 23/24/25-36-43-50/53-68-40
Safety: 28-36/37-45-60-61
Transport Information: UN 1673 6.1/PG 3
PSA: 52.04000
LogP: 2.01340
Synthetic route
99-65-0

meta-dinitrobenzene

108-45-2

m-phenylenediamine

Conditions
ConditionsYield
With sodium tetrahydroborate In water at 20℃; for 1h;100%
With hydrogen; sodium fluoride In methanol at 39.84℃; for 2.17h;100%
With hydrogen In ethanol at 20℃; under 760.051 Torr; for 3h; chemoselective reaction;100%
99-09-2

3-nitro-aniline

108-45-2

m-phenylenediamine

Conditions
ConditionsYield
With C37H23Cl2N7Pd2(2+)*2F6P(1-); hydrogen; sodium cyanoborohydride In methanol at 50℃; under 760.051 Torr; for 6h;100%
With potassium fluoride; polymethylhydrosiloxane; palladium diacetate In tetrahydrofuran; water at 20℃; for 0.5h;99%
With potassium fluoride; polymethylhydrosiloxane; palladium diacetate In tetrahydrofuran at 20℃; for 0.5h;99%
108-36-1

1,3-dibromobenzene

108-45-2

m-phenylenediamine

Conditions
ConditionsYield
With C24H12Cu2F9N4O7; tetrabutylammomium bromide; ammonia; caesium carbonate In water at 110 - 140℃; for 16h;99%
With {(o-C6H4(NCHC6H4O)2)cobalt(II)}2; ammonia at 150℃; under 1500.15 Torr; for 10h; Autoclave; Inert atmosphere; Large scale;73%
With ammonia; water; copper(II) sulfate at 175 - 180℃;
626-00-6

1,3-Diiodobenzene

108-45-2

m-phenylenediamine

Conditions
ConditionsYield
With [Cu2(2,7-bis(pyridin-2-yl)-l,8-naphthyridine)(OH)(CF3COO)3]; tetrabutylammomium bromide; ammonia; caesium carbonate In water at 120℃; for 16h; Sealed tube; chemoselective reaction;99%
With copper(l) iodide; 1,2,4,5-tetramethylbenzene; ammonia at 20℃; for 15h; Reagent/catalyst;94%
1740-57-4

isophthalamide

108-45-2

m-phenylenediamine

Conditions
ConditionsYield
With sodium hypochlorite; water at -5 - 50℃; for 2h; Temperature; Inert atmosphere;97%
With sodium hypochlorite In water at -5 - 50℃; for 4h; Temperature; Hofmann Rearrangement; Inert atmosphere;84.2%
With sodium hypochlorite at 45℃; for 6h; Green chemistry;92 g
With sodium hypochlorite; potassium hydroxide at 0 - 80℃; Hofmann Rearrangement; Inert atmosphere;7.1 g
6283-25-6

H2NC6H3(Cl)NO2

108-45-2

m-phenylenediamine

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrazine hydrate In methanol at 120℃; for 0.25h; Microwave irradiation;96%
108-37-2

1-bromo-3-chlorobenzene

108-45-2

m-phenylenediamine

Conditions
ConditionsYield
With ammonium hydroxide In water at 20℃; for 9h; Green chemistry;96%
14994-81-1

m-aminophenyl azide

108-45-2

m-phenylenediamine

Conditions
ConditionsYield
With hydrazinium monoformate; zinc In methanol at 20℃; for 0.15h;95%

C8H6N2O4(2-)*2K(1+)

108-45-2

m-phenylenediamine

Conditions
ConditionsYield
In water; acetonitrile at 110℃; for 2h;95%
591-19-5

3-bromoaniline

108-45-2

m-phenylenediamine

Conditions
ConditionsYield
With copper(I) oxide; ammonium hydroxide In 1-methyl-pyrrolidin-2-one at 80℃; for 24h;94%
With copper(l) iodide; tetra(n-butyl)ammonium hydroxide; ammonia In water at 80℃; for 48h; Inert atmosphere; Sealed tube; chemoselective reaction;75%
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Consensus Reports

IARC Cancer Review: Group 3 IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 16 ,1978,p. 111.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.

Standards and Recommendations

ACGIH TLV: TWA 0.1 mg/m3; Not Classifiable as a Human Carcinogen
DFG MAK: Confirmed Animal Carcinogen with Unknown Relevance to Humans
DOT Classification:  6.1; Label: KEEP AWAY FROM FOOD

Specification

1,3-Benzenediamine, its cas register number is 108-45-2. It also can be call 1,3-Phenylenediamine; 3-Aminoaniline;
 Benzene, 1,3-diamino-; Metaphenylenediamine; m-Aminoaniline; m-Benzenediamine; m-Diaminobenzene; m-Fenylendiamin; m-Phenylenediamine. 1,3-diaminobenzene, is an organic compound with the formula C6H4(NH2)2. It is an isomer of o-phenylenediamine and p-phenylenediamine. It is a colourless solid. m-Phenylenediamine is produced by hydrogenation of 1,3-dinitrobenzene. The dinitrobenzene is prepared by dinitration of benzene.

Physical properties about 1,3-Benzenediamine are: (1)ACD/LogP: -0.306; (2)ACD/LogD (pH 5.5): -0.40; (3)ACD/LogD (pH 7.4): -0.31; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 13.08; (7)ACD/KOC (pH 7.4): 16.19; (8)#H bond acceptors: 2 ; (9)#H bond donors: 4; (10)#Freely Rotating Bonds: 2; (11)Index of Refraction: 1.66 ; (12)Molar Refractivity: 34.725 cm3; (13)Molar Volume: 93.994 cm3; (14)Polarizability: 13.766 10-24cm3; (15)Surface Tension: 57.5979995727539 dyne/cm; (16)Density: 1.15 g/cm3; (17)Flash Point: 147.572 °C; (18)Enthalpy of Vaporization: 52.208 kJ/mol; (19)Boiling Point: 283.179 °C at 760 mmHg; (20)Vapour Pressure: 0.00300000002607703 mmHg at 25°C

Uses of 1,3-Benzenediamine: 1,3-Benzenediamine is used in the preparation various polymers including aramid fibers, epoxy resins, wire enamel coatings and polyurea elastomers. Other uses for m-phenylenediamine include as an accelerator for adhesive resins, and as a component of dyes for leather and textiles.

When you are using this chemical, please be cautious about it as the following:
1. After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer);
2. Wear suitable protective clothing and gloves;
3. In case of accident or if you feel unwell, seek medical advice immediately (show label where possible);
4. This material and/or its container must be disposed of as hazardous waste;
5. Avoid release to the environment. Refer to special instructions safety data sheet;

You can still convert the following datas into molecular structure:
(1)InChI=1S/C6H8N2/c7-5-2-1-3-6(8)4-5/h1-4H,7-8H2;
(2)InChIKey=WZCQRUWWHSTZEM-UHFFFAOYSA-N;
(3)Smilesc1c(cccc1N)N;

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 562mg/kg (562mg/kg)   Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
 
cat LDLo oral 300mg/kg (300mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Journal of Industrial Hygiene. Vol. 4, Pg. 386, 1923.
dog LDLo intravenous 17mg/kg (17mg/kg)   Journal of Industrial Hygiene. Vol. 4, Pg. 386, 1923.
dog LDLo subcutaneous 100mg/kg (100mg/kg)   National Technical Information Service. Vol. OTS0555804,
guinea pig LD50 oral 450mg/kg (450mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 53(7), Pg. 62, 1988.
guinea pig LD50 unreported 450mg/kg (450mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 31(8), Pg. 46, 1987.
mouse LD50 oral 67700ug/kg (67.7mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 53(7), Pg. 62, 1988.
mouse LD50 subcutaneous 90mg/kg (90mg/kg)   Kyushu Journal of Medical Science. Vol. 13, Pg. 175, 1962.
 
mouse LD50 unreported 65300ug/kg (65.3mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 31(8), Pg. 46, 1987.
mouse LDLo intraperitoneal 400mg/kg (400mg/kg)   Revue Belge de Pathologie et de Medecine Experimentale. Vol. 22, Pg. 1, 1952.
rabbit LD50 oral 437mg/kg (437mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 53(7), Pg. 62, 1988.
rabbit LD50 unreported 438mg/kg (438mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 31(8), Pg. 46, 1987.
rabbit LDLo skin 1500mg/kg (1500mg/kg) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION
National Technical Information Service. Vol. OTS0555804,
rabbit LDLo subcutaneous 200mg/kg (200mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Journal of Industrial Hygiene. Vol. 4, Pg. 386, 1923.
rat LD50 intraperitoneal 283mg/kg (283mg/kg)   Journal of Toxicology and Environmental Health. Vol. 2, Pg. 657, 1977.
 
rat LD50 oral 280mg/kg (280mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 53(7), Pg. 62, 1988.
rat LD50 unreported 351mg/kg (351mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 31(8), Pg. 46, 1987.
rat LDLo subcutaneous 80mg/kg (80mg/kg)   National Technical Information Service. Vol. OTS0555804,

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